EP0900009B1 - Fungicide mixtures - Google Patents

Fungicide mixtures Download PDF

Info

Publication number
EP0900009B1
EP0900009B1 EP97919398A EP97919398A EP0900009B1 EP 0900009 B1 EP0900009 B1 EP 0900009B1 EP 97919398 A EP97919398 A EP 97919398A EP 97919398 A EP97919398 A EP 97919398A EP 0900009 B1 EP0900009 B1 EP 0900009B1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
set forth
iii
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP97919398A
Other languages
German (de)
French (fr)
Other versions
EP0900009A1 (en
Inventor
Ruth Müller
Herbert Bayer
Herbert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Reinhold Saur
Klaus Schelberger
Joachim Leyendecker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to SI9730280T priority Critical patent/SI0900009T1/en
Publication of EP0900009A1 publication Critical patent/EP0900009A1/en
Application granted granted Critical
Publication of EP0900009B1 publication Critical patent/EP0900009B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the invention also relates to methods for combating Harmful fungi with mixtures of the compounds I and / or II and III and the use of the compounds I and / or II and the Compound III for the preparation of such mixtures.
  • IIIa common name: Fenpropimorph, US-A 4,202,894; IIIb: common name: fenpropidin, U.S. 4,202,894; IIIc: common name: tridemorph, DE-A 11 64 152), their preparation and their effect against harmful fungi.
  • DE-A-4309856 discloses fungicidal combinations which are fenpropimorph, fenpropidin or Tridemorph with 2- (2- (6- (2-cyanophenoxy) pyrimidin-4-yloxy) phenyl) -3-methoxyacrylic acid methyl ester contain.
  • the at a reduced total amount of active ingredients applied have an improved effect against harmful fungi (synergistic Mixtures).
  • the general formula I is particularly representative of Oxime ethers in which X is oxygen and Y is CH or X is amino and Y means N.
  • P refers the E / Z isomer mixture or the E isomer is used, the E isomer being particularly preferred.
  • the compounds I can be used both as isomer mixtures and as pure isomers in the mixtures according to the invention. With regard to their use, particular preference is given to compounds I in which the terminal oxime ether grouping of the side chain is in the cis configuration (OCH 3 group to ZR ').
  • Formula II particularly represents carbamates in which the combination of the substituents corresponds to one row of the following table: No. T R n II.1 N 2-F II.2 N 3-F II.3 N 4-F II.4 N 2-Cl II.5 N 3-Cl II.6 N 4-Cl II.7 N 2-Br II.8 N 3-Br II.9 N 4-Br II.10 N 2-CH 3 II.11 N 3-CH 3 II.12 N 4-CH 3 II.13 N 2-CH 2 CH 3 II.14 N 3-CH 2 CH 3 II.15 N 4-CH 2 CH 3 II.16 N 2-CH (CH 3 ) 2 II.17 N 3-CH (CH 3 ) 2 II.18 N 4-CH (CH 3 ) 2 II.19 N 2-CF 3 II.20 N 3-CF 3 II.21 N 4-CF 3 II.22 N 2,4-F 2 II.23 N 2,4-Cl 2 II.24 N 3,4-Cl 2 II.25 N 2-Cl, 4-CH 3 II.26 N 3-Cl, 4-CH 3 II.27 CH 2-F
  • Compounds II.12, II.23, II.32 are particularly preferred and II.38.
  • the compounds I and II are because of the basic character of the NH groups capable of using inorganic or organic Acids or with metal ions to form salts or adducts.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, Sulfuric acid, phosphoric acid and nitric acid.
  • organic acids are formic acid and carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, Trichloroacetic acid and propionic acid as well as glycolic acid, thiocyanic acid, Lactic acid, succinic acid, citric acid, benzoic acid, Cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight chain or branched alkyl radicals with 1 to 20 carbon atoms), Aryl sulfonic acids or disulfonic acids (aromatic residues such as phenyl and naphthyl which have one or two sulfonic acid groups wear), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), Arylphosphonic or diphosphonic acids (aromatic Residues such as phenyl and naphthyl which have one or two phosphoric acid residues wear), the alkyl or aryl radical
  • the ions of the elements of the second main group especially calcium and magnesium
  • the third and fourth main group especially aluminum, tin and lead
  • the first to eighth subgroups in particular. Chromium, manganese, iron, cobalt, nickel, copper, zinc and others in Consideration.
  • the metal ions of the elements are particularly preferred the subgroups of the fourth period.
  • the metals can exist in the different valences that they have.
  • the mixtures of the compounds I and / or II and III or the simultaneous joint or separate use of the Compounds I and / or II and III are distinguished by an excellent Action against a wide range of plant pathogens Mushrooms, especially from the Ascomycetes class, Deuteromycetes, Phycomycetes and Basidiomycetes. they are in some cases. systemically effective and can therefore also as leaf and Soil fungicides are used.
  • the compounds I and / or II and III can be used together at the same time or applied separately or sequentially, wherein the sequence for separate application in general has no effect on the success of the control.
  • the compounds I and / or II and III are usually in a weight ratio of 20: 1 to 0.1: 2, preferably 10: 1 up to 0.2: 1, in particular 5: 1 to 0.5: 1 applied.
  • the application rates in the mixtures according to the invention are in the general depending on the type of effect desired for the Compounds I at 0.01 to 0.5 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • the application rates for the compounds III are correspondingly usually at 0.05 to 1 kg / ha, preferably 0.1 to 1 kg / ha, in particular 0.1 to 0.8 kg / ha.
  • application rates are generally applied Mixture of 0.001 to 50 g / kg seed, preferably 0.01 to 10 g / kg, in particular 0.01 to 5 g / kg used.
  • the fungicidal synergistic mixtures or the compounds I and / or II and III can, for example, in Form of directly sprayable solutions, powders and suspensions or in the form of high-proof aqueous, oily or other Suspensions, dispersions, emulsions, oil dispersions, pastes, Dusts, gritters or granules are processed and by spraying, atomizing, dusting, scattering or pouring be applied.
  • the form of application depends on the intended use; in any case, it should be as fine as possible and ensure uniform distribution of the mixture according to the invention.
  • the formulations are prepared in a manner known per se, eg. by adding solvents and / or carriers.
  • the formulations are usually inert additives such as emulsifiers or dispersants.
  • alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids e.g. Lignin-, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, Condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol or tributylpheny
  • Powders, materials for spreading and dusts can be mixed or combined Grinding of the compounds I and / or II or III or the mixture of the compounds I and / or II and III with a solid carrier.
  • Granules are usually by binding the active ingredient or the active ingredients are produced on a solid carrier.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as cereal flour, tree bark, wood and nutshell flour, Cellulose powder or other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as cereal flour
  • the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of one of the compounds I and / or II and III or the mixture of the compounds I and / or II and III.
  • the active ingredients are in a purity of 90% up to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum) used.
  • the compounds I and / or II or III or the mixtures or the appropriate formulations are applied by: the harmful fungi, the plants, seeds, Floors, surfaces, materials or rooms with a fungicidal effect Amount of the mixture, or of the compounds I and II when separated Output, treated.
  • the application can be before or after infestation by the harmful fungi.
  • the active ingredients are separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and Dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based ethoxylated fatty alcohols) prepared and according to the desired Concentration diluted with water.
  • Nekanil® LN Litensol® AP6, wetting agent with emulsifying and Dispersing action based on ethoxylated alkylphenols
  • Emulphor® EL Emulphor® EL
  • the evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies converted.
  • the expected efficacies of the active ingredient mixtures are based on the Colby formula [R.S. Colby, Weeds 15, 20-22 (1967)] and with the observed efficiencies compared.
  • the infestation corresponds to that treated Plants that of the untreated control plants; at the treated plants do not have an efficiency of 100 Infestation on.

Description

Die vorliegende Erfindung betrifft eine fungizide Mischung, welche

  • a) einen Oximether der Formel I,
    Figure 00010001
    in der die Substituenten die folgende Bedeutung haben:
    X
    Sauerstoff oder Amino (NH);
    Y
    CH oder N;
    Z
    Sauerstoff, Schwefel, Amino (NH) oder C1-C4-Alkylamino (N-C1-C4-Alkyl);
    R'
    C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Alkenyl, C2-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl-methyl, oder Benzyl, welches partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
    und/oder
  • b) ein Carbamat der Formel II,
    Figure 00010002
    in der T CH oder N bedeutet, n für 0, 1 oder 2 steht und R Halogen, C1-C4-Alkyl oder C1-C4-Halogenalkyl bedeutet, wobei die Reste R verschieden sein können, wenn n für 2 steht,
    und
  • c) ein Morpholin- bzw. Piperidinderivat III ausgewählt aus der Gruppe der Verbindungen IIIa, IIIb und IIIc
    Figure 00020001
    Figure 00020002
    Figure 00020003
    in einer synergistisch wirksamen Menge.
    • The present invention relates to a fungicidal mixture which
  • a) an oxime ether of the formula I,
    Figure 00010001
    in which the substituents have the following meaning:
    X
    Oxygen or amino (NH);
    Y
    CH or N;
    Z
    Oxygen, sulfur, amino (NH) or C 1 -C 4 alkylamino (NC 1 -C 4 alkyl);
    R '
    C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl-methyl, or benzyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
    and or
  • b) a carbamate of the formula II,
    Figure 00010002
    in which T is CH or N, n is 0, 1 or 2 and R is halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, where the radicals R can be different if n is 2 .
    and
  • c) a morpholine or piperidine derivative III selected from the group of compounds IIIa, IIIb and IIIc
    Figure 00020001
    Figure 00020002
    Figure 00020003
    in a synergistically effective amount.

    • Außerdem betrifft die Erfindung Verfahren zur Bekämpfung von Schadpilzen mit Mischungen der Verbindungen I und/oder II und III und die Verwendung der Verbindungen I und/oder II und der Verbindung III zur Herstellung derartiger Mischungen.The invention also relates to methods for combating Harmful fungi with mixtures of the compounds I and / or II and III and the use of the compounds I and / or II and the Compound III for the preparation of such mixtures.

    Die Verbindungen der Formel I, ihre Herstellung und ihre Wirkung gegen Schadpilze ist aus der Literatur bekannt (WO-A 95/21,153, WO-A 95/21,154, DE-A 195 28 651.0).The compounds of formula I, their preparation and their action against harmful fungi is known from the literature (WO-A 95 / 21,153, WO-A 95 / 21,154, DE-A 195 28 651.0).

    Verbindungen der Formel II, ihre Herstellung und ihre Wirkung gegen Schadpilze sind in der WO-A 96/01,256 und WO-A 96/01,258 beschrieben.Compounds of formula II, their preparation and their action against harmful fungi are in WO-A 96 / 01,256 and WO-A 96 / 01,258 described.

    Ebenfalls bekannt sind die Morpholin- bzw. Piperidinderivate III (IIIa: common name: Fenpropimorph, US-A 4,202,894; IIIb: common name: Fenpropidin, US-A 4,202,894; IIIc: common name: Tridemorph, DE-A 11 64 152), deren Herstellung und deren Wirkung gegen Schadpilze.The morpholine and piperidine derivatives III are also known (IIIa: common name: Fenpropimorph, US-A 4,202,894; IIIb: common name: fenpropidin, U.S. 4,202,894; IIIc: common name: tridemorph, DE-A 11 64 152), their preparation and their effect against harmful fungi.

    DE-A-4309856 offenbart fungizide Kombinationen die Fenpropimorph, Fenpropidin oder Tridemorph mit 2-(2-(6-(2-Cyanophenoxy)pyrimidin-4-yloxy)-phenyl)-3-methoxyacrylsaüremethylester enthalten. DE-A-4309856 discloses fungicidal combinations which are fenpropimorph, fenpropidin or Tridemorph with 2- (2- (6- (2-cyanophenoxy) pyrimidin-4-yloxy) phenyl) -3-methoxyacrylic acid methyl ester contain.

    Im Hinblick auf eine Senkung der Aufwandmengen und eine Verbesserung des Wirkungsspektrums der bekannten Verbindungen lagen der vorliegenden Erfindungen Mischungen als Aufgabe zugrunde, die bei verringerter Gesamtmenge an ausgebrachten Wirkstoffen eine verbesserte Wirkung gegen Schadpilzen aufweisen (synergistische Mischungen).With a view to reducing the application rates and improving the spectrum of action of the known compounds of the present inventions based on mixtures as an object, the at a reduced total amount of active ingredients applied have an improved effect against harmful fungi (synergistic Mixtures).

    Demgemäß wurden die eingangs definierten Mischungen gefunden. Es wurde außerdem gefunden, daß sich bei gleichzeitiger gemeinsamer oder getrennter Anwendung der Verbindungen I und/oder II und der Verbindungen III oder bei Anwendung der Verbindungen I und/oder II und der Verbindungen III nacheinander Schadpilze besser bekämpfen lassen als mit den Einzelverbindungen.We have found that this object is achieved by the mixtures defined at the outset. It it was also found that, at the same time or separate application of the compounds I and / or II and the Compounds III or when using the compounds I and / or II and the compounds III in succession to combat harmful fungi better leave than with the individual connections.

    Die allgemeine Formel I steht insbesondere repräsentativ für Oximether, in denen X Sauerstoff und Y CH bedeutet oder X Amino und Y N bedeutet.The general formula I is particularly representative of Oxime ethers in which X is oxygen and Y is CH or X is amino and Y means N.

    Außerdem werden Verbindungen I bevorzugt, in denen Z für Sauerstoff steht.In addition, compounds I are preferred in which Z is oxygen stands.

    Gleichermaßen werden Verbindungen I bevorzugt, in denen R' für Alkyl oder Benzyl steht.Likewise preferred are compounds I in which R 'is Is alkyl or benzyl.

    Im Hinblick auf ihre Verwendung in den erfindungsgemäßen synergistischen Mischungen werden insbesondere die in den folgenden Tabellen zusammengestellten Verbindungen I bevorzugt:With regard to their use in the synergistic invention Mixtures are particularly those in the following Compounds I preferred in tables:

    Tabelle 1.Table 1.

    Verbindungen der Formel IA, in denen ZR' für eine Verbindung jeweils einer Zeile der Tabelle A entspricht

    Figure 00030001
    Compounds of the formula IA, in which ZR 'corresponds to one row of Table A for each compound
    Figure 00030001

    Tabelle 2.Table 2.

    Verbindungen der Formel IB, in denen ZR' für eine Verbindung jeweils einer Zeile der Tabelle A entspricht

    Figure 00030002
    Nr. ZR' I.1 O-CH2CH2CH3 I.2 O-CH(CH3)2 I.3 O-CH2CH2CH2CH3 I.4 O-CH(CH3)CH2CH3 I.5 O-CH2CH(CH3)2 I.6 O-C(CH3)3 I.7 S-C(CH3)3 I.8 O-CH(CH3)CH2CH2CH3 I.9 O-CH2C(CH3)3 I.10 O-CH2C(Cl)=CCl2 I.11 O-CH2CH=CH-Cl (trans) I.12 O-CH2C(CH3)=CH2 I.13 O-CH2- (cyclopropyl) I.14 O-CH2-C6H5 I.15 O-CH2-[4-F-C6H4] I.16 O-CH2CH3 I.17 O-CH (CH2CH3)2 Compounds of the formula IB, in which ZR 'corresponds to one row of Table A for each compound
    Figure 00030002
    No. ZR ' I.1 O-CH 2 CH 2 CH 3 I.2 O-CH (CH 3 ) 2 I.3 O-CH 2 CH 2 CH 2 CH 3 I.4 O-CH (CH 3 ) CH 2 CH 3 I.5 O-CH 2 CH (CH 3 ) 2 I.6 OC (CH 3 ) 3 I.7 SC (CH 3 ) 3 I.8 O-CH (CH 3 ) CH 2 CH 2 CH 3 I.9 O-CH 2 C (CH 3 ) 3 I.10 O-CH 2 C (Cl) = CCl 2 I.11 O-CH 2 CH = CH-Cl (trans) I.12 O-CH 2 C (CH 3 ) = CH 2 I.13 O-CH 2 - (cyclopropyl) I.14 O-CH 2 -C 6 H 5 I.15 O-CH 2 - [4-FC 6 H 4 ] I.16 O-CH 2 CH 3 I.17 O-CH (CH 2 CH 3 ) 2

    Die Verbindungen der Formel I können in Bezug auf die C=Y-Doppelbindung in der E- oder der Z-Konfiguration (in Bezug auf die Carbonsäurefunktion) vorliegen. Demgemäß können sie in der erfindungsgemäßen Mischung jeweils entweder als reines E- oder Z-Isomer oder als E/Z-Isomerenmischung Verwendung finden. Bevorzugt findet die E/Z-Isomerenmischung oder das E-Isomer Anwendung, wobei das E-Isomer besonders bevorzugt ist.The compounds of formula I can with respect to the C = Y double bond in the E or Z configuration (in relation to the Carboxylic acid function) are present. Accordingly, they can in the mixture according to the invention either as a pure E or Z isomer or used as an E / Z isomer mixture. Prefers the E / Z isomer mixture or the E isomer is used, the E isomer being particularly preferred.

    Die C=N-Doppelbindungen der Oximethergruppierungen in der Seitenkette der Verbindungen I können jeweils als reine E- oder Z-Isomere oder als E/Z-Isomerengemische vorliegen. Die Verbindungen I können sowohl als Isomerengemische als auch als reine Isomere in den erfindungsgemäßen Mischungen verwendet werden. Im Hinblick auf ihre Verwendung werden insbesondere Verbindungen I bevorzugt, in denen die endständige Oximethergruppierung der Seitenkette in der cis-Konfiguration vorliegt (OCH3Gruppe zu ZR').The C = N double bonds of the oxime ether groups in the side chain of the compounds I can each be present as pure E or Z isomers or as E / Z isomer mixtures. The compounds I can be used both as isomer mixtures and as pure isomers in the mixtures according to the invention. With regard to their use, particular preference is given to compounds I in which the terminal oxime ether grouping of the side chain is in the cis configuration (OCH 3 group to ZR ').

    Die Formel II repräsentiert insbesondere Carbamate, in denen die Kombination der Substituenten einer Zeile der folgenden Tabelle entspricht: Nr. T Rn II.1 N 2-F II.2 N 3-F II.3 N 4-F II.4 N 2-Cl II.5 N 3-Cl II.6 N 4-Cl II.7 N 2-Br II.8 N 3-Br II.9 N 4-Br II.10 N 2-CH3 II.11 N 3-CH3 II.12 N 4-CH3 II.13 N 2-CH2CH3 II.14 N 3-CH2CH3 II.15 N 4-CH2CH3 II.16 N 2-CH(CH3)2 II.17 N 3-CH(CH3)2 II.18 N 4-CH(CH3)2 II.19 N 2-CF3 II.20 N 3-CF3 II.21 N 4-CF3 II.22 N 2,4-F2 II.23 N 2,4-Cl2 II.24 N 3,4-Cl2 II.25 N 2-Cl, 4-CH3 II.26 N 3-Cl, 4-CH3 II.27 CH 2-F II.28 CH 3-F II.29 CH 4-F II.30 CH 2-Cl II.31 CH 3-Cl II.32 CH 4-Cl II.33 CH 2-Br II.34 CH 3-Br II.35 CH 4-Br II.36 CH 2-CH3 II.37 CH 3-CH3 II.38 CH 4-CH3 II.39 CH 2-CH2CH3 II.40 CH 3-CH2CH3 II.41 CH 4-CH2CH3 II.42 CH 2-CH(CH3)2 II.43 CH 3-CH(CH3)2 II.44 CH 4-CH(CH3)2 II.45 CH 2-CF3 II.46 CH 3-CF3 II.47 CH 4-CF3 II.48 CH 2,4-F2 II.49 CH 2,4-Cl2 II.50 CH 3,4-Cl2 II.51 CH 2-Cl, 4-CH3 II.52 CH 3-Cl, 4-CH3 Formula II particularly represents carbamates in which the combination of the substituents corresponds to one row of the following table: No. T R n II.1 N 2-F II.2 N 3-F II.3 N 4-F II.4 N 2-Cl II.5 N 3-Cl II.6 N 4-Cl II.7 N 2-Br II.8 N 3-Br II.9 N 4-Br II.10 N 2-CH 3 II.11 N 3-CH 3 II.12 N 4-CH 3 II.13 N 2-CH 2 CH 3 II.14 N 3-CH 2 CH 3 II.15 N 4-CH 2 CH 3 II.16 N 2-CH (CH 3 ) 2 II.17 N 3-CH (CH 3 ) 2 II.18 N 4-CH (CH 3 ) 2 II.19 N 2-CF 3 II.20 N 3-CF 3 II.21 N 4-CF 3 II.22 N 2,4-F 2 II.23 N 2,4-Cl 2 II.24 N 3,4-Cl 2 II.25 N 2-Cl, 4-CH 3 II.26 N 3-Cl, 4-CH 3 II.27 CH 2-F II.28 CH 3-F II.29 CH 4-F II.30 CH 2-Cl II.31 CH 3-Cl II.32 CH 4-Cl II.33 CH 2-Br II.34 CH 3-Br II.35 CH 4-Br II.36 CH 2-CH 3 II.37 CH 3-CH 3 II.38 CH 4-CH 3 II.39 CH 2-CH 2 CH 3 II.40 CH 3-CH 2 CH 3 II.41 CH 4-CH 2 CH 3 II.42 CH 2-CH (CH 3 ) 2 II.43 CH 3-CH (CH 3 ) 2 II.44 CH 4-CH (CH 3 ) 2 II.45 CH 2-CF 3 II.46 CH 3-CF 3 II.47 CH 4-CF 3 II.48 CH 2,4-F 2 II.49 CH 2,4-Cl 2 II.50 CH 3,4-Cl 2 II.51 CH 2-Cl, 4-CH 3 II.52 CH 3-Cl, 4-CH 3

    Besonders bevorzugt werden die Verbindungen II.12, II.23, II.32 und II.38.Compounds II.12, II.23, II.32 are particularly preferred and II.38.

    Die Verbindungen I und II sind wegen des basischen Charakters der NH-Gruppen in der Lage, mit anorganischen oder organischen Säuren oder mit Metallionen Salze oder Addukte zu bilden.The compounds I and II are because of the basic character of the NH groups capable of using inorganic or organic Acids or with metal ions to form salts or adducts.

    Beispiele für anorganische Säuren sind Halogenwasserstoffsäuren wie Fluorwasserstoff, Chlorwasserstoff, Bromwasserstoff und Jodwasserstoff, Schwefelsäure, Phosphorsäure und Salpetersäure.Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, Sulfuric acid, phosphoric acid and nitric acid.

    Als organische Säuren kommen beispielsweise Ameisensäure, Kohlensäure und Alkansäuren wie Essigsäure, Trifluoressigsäure, Trichloressigsäure und Propionsäure sowie Glycolsäure, Thiocyansäure, Milchsäure, Bernsteinsäure, Zitronensäure, Benzoesäure, Zimtsäure, Oxalsäure, Alkylsulfonsäuren (Sulfonsäuren mit geradkettigen oder verzweigten Alkylresten mit 1 bis 20 Kohlenstoffatomen), Arylsulfonsäuren oder -disulfonsäuren (aromatische Reste wie Phenyl und Naphthyl welche eine oder zwei Sulfonsäuregruppen tragen), Alkylphosphonsäuren (Phosphonsäuren mit geradkettigen oder verzweigten Alkylresten mit 1 bis 20 Kohlenstoffatomen), Arylphosphonsäuren oder -diphosphonsäuren (aromatische Reste wie Phenyl und Naphthyl welche eine oder zwei Phosphorsäurereste tragen), wobei die Alkyl- bzw. Arylreste weitere Substituenten tragen können, zB. p-Toluolsulfonsäure, Salizylsäure, p-Aminosalizylsäure, 2-Phenoxybenzoesäure, 2-Acetoxybenzoesäure etc., in Betracht. Examples of organic acids are formic acid and carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, Trichloroacetic acid and propionic acid as well as glycolic acid, thiocyanic acid, Lactic acid, succinic acid, citric acid, benzoic acid, Cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight chain or branched alkyl radicals with 1 to 20 carbon atoms), Aryl sulfonic acids or disulfonic acids (aromatic residues such as phenyl and naphthyl which have one or two sulfonic acid groups wear), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), Arylphosphonic or diphosphonic acids (aromatic Residues such as phenyl and naphthyl which have one or two phosphoric acid residues wear), the alkyl or aryl radicals further substituents can wear, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid etc., into consideration.

    Als Metallionen kommen insbesondere die Ionen der Elemente der zweiten Hauptgruppe, insbesondere Calzium und Magnesium, der dritten und vierten Hauptgruppe, insbesondere Aluminium, Zinn und Blei, sowie der ersten bis achten Nebengruppe, insbesondere. Chrom, Mangan, Eisen, Kobalt, Nickel, Kupfer, Zink und andere in Betracht. Besonders bevorzugt sind die Metallionen der Elemente der Nebengruppen der vierten Periode. Die Metalle können dabei in den verschiedenen ihnen zukommenden Wertigkeiten vorliegen.In particular, the ions of the elements of the second main group, especially calcium and magnesium, the third and fourth main group, especially aluminum, tin and lead, and the first to eighth subgroups, in particular. Chromium, manganese, iron, cobalt, nickel, copper, zinc and others in Consideration. The metal ions of the elements are particularly preferred the subgroups of the fourth period. The metals can exist in the different valences that they have.

    Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und/oder II und III ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schadpilze oder andere Schädlinge wie Insekten, Spinntiere oder Nematoden, oder auch herbizide oder wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann.It is preferred to use the when preparing the mixtures pure active ingredients I and / or II and III, which one depending on Need more agents against harmful fungi or other pests such as insects, arachnids or nematodes, or also herbicidal or growth-regulating active ingredients or fertilizers can mix.

    Die Mischungen der Verbindungen I und/oder II und III bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der Verbindungen I und/oder II und III zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Deuteromyceten, Phycomyceten und Basidiomyceten, aus. Sie sind zT. systemisch wirksam und können daher auch als Blatt- und Bodenfungizide eingesetzt werden.The mixtures of the compounds I and / or II and III or the simultaneous joint or separate use of the Compounds I and / or II and III are distinguished by an excellent Action against a wide range of plant pathogens Mushrooms, especially from the Ascomycetes class, Deuteromycetes, Phycomycetes and Basidiomycetes. they are in some cases. systemically effective and can therefore also as leaf and Soil fungicides are used.

    Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (zB. Gurken, Bohnen und Kürbisgewächse), Gerste, Gras, Hafer, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen.They are particularly important for combating a large number of mushrooms on various crops such as cotton, vegetables (e.g. cucumber, beans and squash), barley, Grass, oats, coffee, corn, fruit plants, rice, rye, soy, Wine, wheat, ornamental plants, sugar cane and a variety of Seeds.

    Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuckerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminchosporium-Arten an Getreide, Rhynosporium Secalis, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudocercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Alternaria-Arten an Gemüse und Obst sowie Fusarium- und Verticillium-Arten. In particular, they are suitable for combating the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) Cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea Pumpkin family, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawn, Ustilago on cereals and Sugar cane, Venturia inaequalis (scab) on apples, Helminchosporium species on cereals, Rhynosporium Secalis, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, Ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Alternaria species Vegetables and fruits as well as Fusarium and Verticillium species.

    Sie sind außerdem im Materialschutz (z.B. Holzschutz) anwendbar, beispielsweise gegen Paecilomyces variotii.They can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.

    Die Verbindungen I und/oder II und III können gleichzeitig gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compounds I and / or II and III can be used together at the same time or applied separately or sequentially, wherein the sequence for separate application in general has no effect on the success of the control.

    Die Verbindungen I und/oder II und III werden üblicherweise in einem Gewichtsverhältnis von 20:1 bis 0.1:2, vorzugsweise 10:1 bis 0.2:1, insbesondere 5:1 bis 0.5:1 angewendet.The compounds I and / or II and III are usually in a weight ratio of 20: 1 to 0.1: 2, preferably 10: 1 up to 0.2: 1, in particular 5: 1 to 0.5: 1 applied.

    Die Aufwandmengen in den erfindungsgemäßen Mischungen liegen im allgemeinen je nach Art des gewünschten Effekts für die Verbindungen I bei 0,01 bis 0,5 kg/ha, vorzugsweise 0,05 bis 0,5 kg/ha, insbesondere 0,05 bis 0,3 kg/ha.The application rates in the mixtures according to the invention are in the general depending on the type of effect desired for the Compounds I at 0.01 to 0.5 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.

    Die Aufwandmengen für die Verbindungen III liegen entsprechend üblicherweise bei 0,05 bis 1 kg/ha, vorzugsweise 0,1 bis 1 kg/ha, insbesondere 0,1 bis 0,8 kg/ha.The application rates for the compounds III are correspondingly usually at 0.05 to 1 kg / ha, preferably 0.1 to 1 kg / ha, in particular 0.1 to 0.8 kg / ha.

    Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 50 g/kg Saatgut, vorzugsweise 0,01 bis 10 g/kg, insbesondere 0,01 bis 5 g/kg verwendet.When treating seeds, application rates are generally applied Mixture of 0.001 to 50 g / kg seed, preferably 0.01 to 10 g / kg, in particular 0.01 to 5 g / kg used.

    Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind, erfolgt die getrennte oder gemeinsame Applikation der Verbindungen I und/oder Ii und III oder der Mischungen aus den Verbindungen I und/oder II und III durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.If pathogenic harmful fungi have to be combated for plants, this is done the separate or joint application of the connections I and / or Ii and III or the mixtures of the compounds I and / or II and III by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.

    Die erfindungsgemäßen fungiziden synergistischen Mischungen bzw. die Verbindungen I und/oder II und III können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten. The fungicidal synergistic mixtures or the compounds I and / or II and III can, for example, in Form of directly sprayable solutions, powders and suspensions or in the form of high-proof aqueous, oily or other Suspensions, dispersions, emulsions, oil dispersions, pastes, Dusts, gritters or granules are processed and by spraying, atomizing, dusting, scattering or pouring be applied. The form of application depends on the intended use; in any case, it should be as fine as possible and ensure uniform distribution of the mixture according to the invention.

    Die Formulierungen werden in an sich bekannter Weise hergestellt, zB. durch Zugabe von Lösungsmitteln und/oder Trägerstoffen. Den Formulierungen werden üblicherweise inerte Zusatzstoffe wie Emulgiermittel oder Dispergiermittel beigemischt.The formulations are prepared in a manner known per se, eg. by adding solvents and / or carriers. The formulations are usually inert additives such as emulsifiers or dispersants.

    Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolethern, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol- oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid- Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxypropylen, Laurylalkoholpolyglycoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. Lignin-, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, Condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol or tributylphenyl polyglycol ether, Alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide Condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite liquors or methyl cellulose into consideration.

    Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der Verbindungen I und/oder II oder III oder der Mischung aus den Verbindungen I und/oder II und III mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or combined Grinding of the compounds I and / or II or III or the mixture of the compounds I and / or II and III with a solid carrier.

    Granulate (zB. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g. coating, impregnation or homogeneous granules) are usually by binding the active ingredient or the active ingredients are produced on a solid carrier.

    Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Kalzium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Serve as fillers or solid carriers, for example Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as cereal flour, tree bark, wood and nutshell flour, Cellulose powder or other solid carriers.

    Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen I und/oder II und III bzw. der Mischung aus den Verbindungen I und/oder II und III. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100 %, vorzugsweise 95 % bis 100 % (nach NMR- oder HPLC-Spektrum) eingesetzt. The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of one of the compounds I and / or II and III or the mixture of the compounds I and / or II and III. The active ingredients are in a purity of 90% up to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum) used.

    Die Verbindungen I und/oder II oder III bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und II bei getrennter Ausbringung, behandelt. Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The compounds I and / or II or III or the mixtures or the appropriate formulations are applied by: the harmful fungi, the plants, seeds, Floors, surfaces, materials or rooms with a fungicidal effect Amount of the mixture, or of the compounds I and II when separated Output, treated. The application can be before or after infestation by the harmful fungi.

    Die fungizide Wirkung der Verbindungen und der Mischungen läßt sich durch folgende Versuche zeigen:The fungicidal activity of the compounds and the mixtures leaves are shown by the following experiments:

    Die Wirkstoffe werden getrennt oder gemeinsam als 10 %-ige Emulsion in einem Gemisch aus 70 Gew.-% Cyclohexanon, 20 Gew.-% Nekanil® LN (Lutensol® AP6, Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) und 10 Gew.-% Emulphor® EL (Emulan® EL, Emulgator auf der Basis ethoxylierter Fettalkohole) aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active ingredients are separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and Dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based ethoxylated fatty alcohols) prepared and according to the desired Concentration diluted with water.

    Die Auswertung erfolgt durch Feststellung der befallenen Blattflächen in Prozent. Diese Prozent-Werte werden in Wirkungsgrade umgerechnet. Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen werden nach der Colby Formel [R.S. Colby, Weeds 15, 20-22 (1967)] ermittelt und mit den beobachteten Wirkungsgraden verglichen.The evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies converted. The expected efficacies of the active ingredient mixtures are based on the Colby formula [R.S. Colby, Weeds 15, 20-22 (1967)] and with the observed efficiencies compared.

    Colby Formel: E = x + y - x·y/100

    E
    zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b
    x
    der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a
    y
    der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration b
    Colby formula: E = x + y - xy / 100
    e
    expected efficiency, expressed in% of the untreated control, when using the mixture of active ingredients A and B in concentrations a and b
    x
    the degree of effectiveness, expressed in% of the untreated control, when using the active ingredient A in the concentration a
    y
    the efficiency, expressed in% of the untreated control, when using the active ingredient B in the concentration b

    Der Wirkungsgrad ( W ) wird nach der Formel von Abbot wie folgt berechnet: W = (1 - α)•100/β

    α
    entspricht dem Pilzbefall der behandelten Pflanzen in % und
    β
    entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %
    Efficiency ( W ) is calculated using Abbot's formula as follows: W = (1 - α) • 100 / β
    α
    corresponds to the fungal attack of the treated plants in% and
    β
    corresponds to the fungal attack of the untreated (control) plants in%

    Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 weisen die behandelten Pflanzen keinen Befall auf.With an efficiency of 0, the infestation corresponds to that treated Plants that of the untreated control plants; at the treated plants do not have an efficiency of 100 Infestation on.

    Beispiele 1 - 7Examples 1-7 Wirksamkeit gegen WeizenmehltauEfficacy against powdery mildew

    Blätter von in Töpfen gewachsenen Weizenkeimlingen der Sorte "Frühgold" wurden mit wäßriger Wirkstoffaufbereitung, die aus einer Stammlösung bestehend aus 10 % Wirkstoff. 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, bis zur Tropfnäße besprüht und 24 Stunden nach dem Antrocknen des Spritzbelages mit Sporen des Weizenmehltaus (Erysiphe graminis forma specialis tritici) bestäubt. Die Versuchspflanzen wurden anschließend im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 80 % relativer Luftfeuchtigkeit aufgestellt. Nach 7 Tagen wurde das Ausmaß der Mehltauentwicklung visuell in % Befall der gesamten Blattfläche ermittelt.Leaves of potted wheat seedlings of the variety "Early gold" were made with aqueous active ingredient preparation a stock solution consisting of 10% active ingredient. 63% cyclohexanone and 27% emulsifier was added until dripping wet sprayed and 24 hours after the spray coating has dried on with spores of powdery mildew (Erysiphe graminis forma specialis tritici) pollinated. The test plants were then in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. To For 7 days, the extent of mildew development was visually affected in% of the entire leaf area determined.

    Die visuell ermittelten Werte für den Prozentanteil befallener Blattfäche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S.R. (Calculating synergistic and antagonistic respeonses of herbicide Combinations", Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen. Bsp. Wirkstoff Wirkstoffkonzentration in der Spritzbrühe in ppm Wirkungsgrad in % der unbehandelten Kontrolle 1V Kontrolle (unbehandelt) (97 % Befall) 0 2V A = Tab. 1A,
    Nr. 2     1 90     3V B = Tab. 1A,
    Nr. 4     16 85     4V IIIa = Fenpropimorph 1 0 5V IIIc = Tridemorph 16 0     Bsp. Wirkstoffkonzentration in der Spritzbrühe in ppm beobachteter Wirkstoff berechneter Wirkungsgrad 6 1 A + 1 IIIa 100 90 7 16 B + 16 IIIc 100 85     The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active ingredients were determined using the Colby formula (Colby, SR (Calculating synergistic and antagonistic respeonses of herbicide combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies. E.g. active substance Active ingredient concentration in the spray mixture in ppm Efficiency in% of the untreated control 1V Control (untreated) (97% infestation) 0 2V A = Tab. 1A,
    No. 2     1 90     3V B = Tab. 1A,
    No. 4     16 85     4V IIIa = fenpropimorph 1 0 5V IIIc = tridemorph 16 0     E.g. Active ingredient concentration in the spray mixture in ppm observed drug calculated efficiency 6 1 A + 1 IIIa 100 90 7 16 B + 16 IIIc 100 85

    Beispiele 8 - 17Examples 8-17 Wirksamkeit gegen Puccinia recondita an WeizenEfficacy against Puccinia recondita on wheat (Weizenbraunrost)(Wheat brown rust)

    Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Frühgold" wurden mit Sporen des Braunrostes (Puccinia recondita) bestäubt. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 22°C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit einer wäßrigen Wirkstoffaufbereitung, die aus einer Stammlösung bestehend aus 10% Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt worden war, tropfnaß besprüht. Nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern ermittelt.Leaves of potted wheat seedlings of the variety "Early gold" were made with spores of the brown rust (Puccinia recondita) pollinated. After that, the pots were placed in one for 24 hours Chamber with high humidity (90 to 95%) and 20 to 22 ° C posed. During this time the spores germinated and the Germ tubing penetrated the leaf tissue. The infected Plants were treated the next day with an aqueous active ingredient preparation, which consists of a stock solution consisting of 10% active ingredient, 63% cyclohexanone and 27% emulsifier were used was sprayed soaking wet. After the spray coating has dried on were the test plants in the greenhouse at temperatures between 20 and 22 ° C and 65 to 70% relative humidity cultivated for 7 days. Then the extent of rust fungus development determined on the leaves.

    Die visuell ermittelten Werte für den Prozentanteil befallener Blattfäche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S.R. (Calculating synergistic and antagonistic respeonses of herbicide Combinations", Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen. Bsp. Wirkstoff Wirkstoffkonzentration in der Spritzbrühe in ppm Wirkungsgrad in % der unbehandelten Kontrolle 8V Kontrolle (unbehandelt) (100 % Befall) 0 9V A = Tab. 1A,
    Nr. 2     4 20     10V B = Tab. 1A,
    Nr. 4     4 80     11V IIIa = Fenpropimorph 4 20 12V IIIb = Fenpropidin 4 0 13V IIIc = Tridemorph 4 0     Bsp. Wirkstoffkonzentration in der Spritzbrühe in ppm beobachteter Wirkstoff berechneter Wirkungsgrad 14 4 A + 4 IIIa 99 36 15 4 A + 4 IIIb 50 20 16 4 A + 4 IIIc 90 20 17 4 B + 4 IIIa 100 84     The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active ingredients were determined using the Colby formula (Colby, SR (Calculating synergistic and antagonistic respeonses of herbicide combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies. E.g. active substance Active ingredient concentration in the spray mixture in ppm Efficiency in% of the untreated control 8V Control (untreated) (100% infestation) 0 9V A = Tab. 1A,
    No. 2     4 20     10V B = Tab. 1A,
    No. 4     4 80     11V IIIa = fenpropimorph 4 20 12V IIIb = fenpropidine 4 0 13V IIIc = tridemorph 4 0     E.g. Active ingredient concentration in the spray mixture in ppm observed drug calculated efficiency 14 4 A + 4 IIIa 99 36 15 4 A + 4 IIIb 50 20 16 4 A + 4 IIIc 90 20 17 4 B + 4 IIIa 100 84

    Beispiele 18 - 28Examples 18-28 Wirksamkeit gegen WeizenmehltauEfficacy against powdery mildew

    Blätter von in Töpfen gewachsenen Weizenkeimlingen der Sorte "Frühgold" wurden mit wäßriger Wirkstoffaufbereitung, die aus einer Stammlösung bestehend aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, bis zur Tropfnäße besprüht und 24 Stunden nach dem Antrocknen des Spritzbelages mit Sporen des Weizenmehltaus (Erysiphe graminis formaspecialis tritici) bestäubt. Die Versuchspflanzen wurden anschließend im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 80 % relativer Luftfeuchtigkeit aufgestellt. Nach 7 Tagen wurde das Ausmaß der Mehltauentwicklung visuell in % Befall der gesamten Blattfläche ermittelt.Leaves of potted wheat seedlings of the variety "Early gold" were made with aqueous active ingredient preparation a stock solution consisting of 10% active ingredient, 63% cyclohexanone and 27% emulsifier was added until dripping wet sprayed and 24 hours after the spray coating has dried on with spores of powdery mildew (Erysiphe graminis formaspecialis tritici) pollinated. The test plants were then in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. To For 7 days, the extent of mildew development was visually affected in% of the entire leaf area determined.

    Die visuell ermittelten Werte für den Prozentanteil befallener Blattfäche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S.R. (Calculating synergistic and antagonistic respeonses of herbicide Combinations", Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen. Bsp. Wirkstoff Wirkstoffkonzentration in der Spritzbrühe in ppm Wirkungsgrad in % der unbehandelten Kontrolle 18V Kontrolle (unbehandelt) (97 % Befall) 0 19V C = Verbindung Nr. II.32 in Tabelle 3 16
    4
    1     90
    85
    17         20V D = Verbindung Nr. II.38 in Tabelle 3 1 7 21V IIIa = Fenpropimorph 1 0 22V IIIb = Fenpropidin 1 7 23V IIIc = Tridemorph 16
    4     0
    0         Bsp. Wirkstoffkonzentration in der Spritzbrühe in ppm beobachteter Wirkstoff berechneter Wirkungsgrad 24 1 C + 1 IIIa 85 17 25 1 C + 1 IIIb 38 23 26 16 C + 16 IIIc 100 90 27 4 C + 4 IIIc 93 85 28 1 D + 1 IIIb 35 14     The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active ingredients were determined using the Colby formula (Colby, SR (Calculating synergistic and antagonistic respeonses of herbicide combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies. E.g. active substance Active ingredient concentration in the spray mixture in ppm Efficiency in% of the untreated control 18V Control (untreated) (97% infestation) 0 19V C = Compound No. II.32 in Table 3 16
    4
    1     90
    85
    17     20V D = Compound No. II.38 in Table 3 1 7 21V IIIa = fenpropimorph 1 0 22V IIIb = fenpropidine 1 7 23V IIIc = tridemorph 16
    4     0
    0     E.g. Active ingredient concentration in the spray mixture in ppm observed drug calculated efficiency 24 1 C + 1 IIIa 85 17 25 1 C + 1 IIIb 38 23 26 16 C + 16 IIIc 100 90 27 4 C + 4 IIIc 93 85 28 1 D + 1 IIIb 35 14

    Beispiele 29 - 39Examples 29-39 Wirksamkeit gegen Puccinia recondita an WeizenEfficacy against Puccinia recondita on wheat (Weizenbraunrost)(Wheat brown rust)

    Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Frühgold" wurden mit Sporen des Braunrostes (Puccinia recondita) bestäubt. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 22°C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit einer wäßrigen Wirkstoffaufbereitung, die aus einer Stammlösung bestehend aus 10% Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt worden war, tropfnaß besprüht. Nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern ermittelt.Leaves of potted wheat seedlings of the variety "Early gold" were made with spores of the brown rust (Puccinia recondita) pollinated. After that, the pots were placed in one for 24 hours Chamber with high humidity (90 to 95%) and 20 to 22 ° C posed. During this time the spores germinated and the Germ tubing penetrated the leaf tissue. The infected Plants were treated the next day with an aqueous active ingredient preparation, which consists of a stock solution consisting of 10% active ingredient, 63% cyclohexanone and 27% emulsifier were used was sprayed soaking wet. After the spray coating has dried on were the test plants in the greenhouse at temperatures between 20 and 22 ° C and 65 to 70% relative humidity cultivated for 7 days. Then the extent of rust fungus development determined on the leaves.

    Die visuell ermittelten Werte für den Prozentanteil befallener Blattfäche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S.R. (Calculating synergistic and antagonistic respeonses of herbicide Combinations", Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.

    Figure 00160001
    The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active ingredients were determined using the Colby formula (Colby, SR (Calculating synergistic and antagonistic respeonses of herbicide combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies.
    Figure 00160001

    Die Ergebnisse der Versuche 1-39 zeigen, daß der beobachtete Wirkungsgrad in allen Mischungsverhältnissen höher ist als der nach der Colby-Formel vorausberechnete Wirkungsgrad.The results of experiments 1-39 show that the observed Efficiency is higher than that in all mixing ratios Efficiency calculated in advance according to the Colby formula.

    Claims (9)

    1. A fungicidal mixture comprising
      a) an oxime ether of the formula I
      Figure 00200001
      where the substi uents have the following meanings:
      X
      is oxygen or amino (NH);
      Y
      is CH or N;
      Z
      is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N-C1-C4-alkyl);
      R'
      is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio and/or
      b) a carbamate of the formula II
      Figure 00210001
      where T is CH or N, n is 0, 1 or 2 and R is halogen, C1-C4-alkyl or C1-C4-haloalkyl, it being possible for the radicals R to be different if n is 2,
      and
      c) a morpholine or piperidine derivative III selected from the group of the compounds IIIa, IIIb and IIIc
      Figure 00210002
      Figure 00210003
      Figure 00210004
      in a synergistically active amount.
    2. A fungicidal mixture as claimed in claim 1 comprising an oxime ether of the formula I and/or a carbamate of the formula II as set forth in claim 1 and the morpholine derivative IIIa.
    3. A fungicidal mixture as claimed in claim 1 comprising an oxime ether of the formula I and/or a carbamate of the formula II as set forth in claim 1 and the piperidine derivative IIIb.
    4. A fungicidal mixture as claimed in claim 1 comprising an oxime ether of the formula I and/or a carbamate of the formula II as set forth in claim 1 and the morpholine derivative IIIc.
    5. A fungicidal mixture as claimed in claim 1 wherein the weight ratio of the compound I and/or II to the compound III is 20:1 to 0.1:2.
    6. A method of controlling harmful fungi, which comprises treating the harmful fungi, their environment, or the plants, seeds, soils, areas, materials or spaces to be kept free from them with a compound of the formula I and/or a compound of the formula II in a synergistically active amount as set forth in claim 1 and the compound of the formula III as set forth in claim 1.
    7. A method as claimed in claim 6, wherein a compound I and/or a compound of the formula II as set forth in claim 1 and a compound III as set forth in claim 1 are applied simultaneously together or separately or in succession.
    8. A method as claimed in claim 6, wherein the harmful fungi, their environment, or the plants, seeds, soils, areas, materials or spaces to be kept free from them are treated with from 0.01 to 0.5 kg/ha of a compound I and/or a compound of the formula II as set forth in claim 1.
    9. A method as claimed in claim 6, wherein the harmful fungi, their environment, or the plants, seeds, soils, areas, materials or spaces to be kept free from them are treated with from 0.05 to 1 kg/ha of a compound III as set forth in claim 1.
    EP97919398A 1996-04-26 1997-04-22 Fungicide mixtures Expired - Lifetime EP0900009B1 (en)

    Priority Applications (1)

    Application Number Priority Date Filing Date Title
    SI9730280T SI0900009T1 (en) 1996-04-26 1997-04-22 Fungicide mixtures

    Applications Claiming Priority (7)

    Application Number Priority Date Filing Date Title
    DE19616724 1996-04-26
    DE19616724 1996-04-26
    DE19617232 1996-04-30
    DE19617232 1996-04-30
    DE19635511 1996-09-02
    DE19635511 1996-09-02
    PCT/EP1997/002015 WO1997040673A1 (en) 1996-04-26 1997-04-22 Fungicide mixtures

    Publications (2)

    Publication Number Publication Date
    EP0900009A1 EP0900009A1 (en) 1999-03-10
    EP0900009B1 true EP0900009B1 (en) 2002-03-27

    Family

    ID=27216191

    Family Applications (1)

    Application Number Title Priority Date Filing Date
    EP97919398A Expired - Lifetime EP0900009B1 (en) 1996-04-26 1997-04-22 Fungicide mixtures

    Country Status (26)

    Country Link
    US (1) US6136802A (en)
    EP (1) EP0900009B1 (en)
    JP (1) JP4170393B2 (en)
    KR (1) KR100432453B1 (en)
    CN (1) CN1106148C (en)
    AR (1) AR006863A1 (en)
    AT (1) ATE214874T1 (en)
    AU (1) AU734568B2 (en)
    BR (1) BR9708874A (en)
    CA (1) CA2252523C (en)
    CO (1) CO4761034A1 (en)
    CZ (1) CZ291462B6 (en)
    DE (1) DE59706770D1 (en)
    DK (1) DK0900009T3 (en)
    EA (1) EA001006B1 (en)
    ES (1) ES2175396T3 (en)
    HU (1) HU225630B1 (en)
    IL (1) IL126083A (en)
    NZ (1) NZ331766A (en)
    PL (1) PL187549B1 (en)
    PT (1) PT900009E (en)
    SI (1) SI0900009T1 (en)
    SK (1) SK282795B6 (en)
    TW (1) TW347311B (en)
    UA (1) UA56167C2 (en)
    WO (1) WO1997040673A1 (en)

    Families Citing this family (9)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    NZ331766A (en) * 1996-04-26 2000-04-28 Basf Ag Fungicide mixtures comprising an oxime ether, a carbamate and a morpholine or pyridine derivative
    EP1009235A1 (en) 1997-06-04 2000-06-21 Basf Aktiengesellschaft Fungicidal mixtures
    EP0986304B1 (en) 1997-06-04 2002-07-24 Basf Aktiengesellschaft Fungicidal mixture
    UA72490C2 (en) * 1998-12-22 2005-03-15 Басф Акцієнгезелльшафт Fungicidal mixture and a method of controlling phytopathogenic fungi
    OA12957A (en) * 2002-11-15 2006-10-13 Basf Ag Fungicidal mixtures.
    US9172139B2 (en) 2009-12-03 2015-10-27 Apple Inc. Bezel gap antennas
    US9160056B2 (en) 2010-04-01 2015-10-13 Apple Inc. Multiband antennas formed from bezel bands with gaps
    CN102919254A (en) * 2010-12-08 2013-02-13 陕西美邦农药有限公司 Fungicide composition containing tridemorph
    US8947303B2 (en) 2010-12-20 2015-02-03 Apple Inc. Peripheral electronic device housing members with gaps and dielectric coatings

    Family Cites Families (12)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    AT354187B (en) * 1976-11-22 1979-12-27 Hoffmann La Roche FUNGICIDE AGENT
    DE4124255A1 (en) * 1991-07-22 1993-01-28 Basf Ag FUNGICIDAL MIXTURE
    DE4309856A1 (en) * 1993-03-26 1994-09-29 Basf Ag Fungicidal mixture
    EP0645087B1 (en) * 1993-09-24 1996-04-17 BASF Aktiengesellschaft Fungicidal mixtures
    EP0737421A4 (en) * 1993-12-27 1998-09-02 Sumitomo Chemical Co Bactericidal composition
    DK0738259T3 (en) * 1994-02-04 2000-09-18 Basf Ag Phenylacetic acid derivatives, processes and intermediates for their preparation and agents containing them
    PL179345B1 (en) * 1994-02-04 2000-08-31 Basf Ag Derivatives of phenyloacetic acid, method of and intermediate products for obtaining them and agents containing such derivatives
    DE4423613A1 (en) * 1994-07-06 1996-01-11 Basf Ag 2- [1 ', 2', 4'-triazole-3'yloxymethylene] anilides, process for their preparation and their use
    DE4423612A1 (en) * 1994-07-06 1996-01-11 Basf Ag 2 - [(Dihydro) pyrazolyl-3'-oxymethylene] anilides, process for their preparation and their use
    DE19528651A1 (en) * 1995-08-04 1997-02-06 Basf Ag Hydroximic acid derivatives, process for their preparation and compositions containing them
    WO1997006681A1 (en) * 1995-08-17 1997-02-27 Basf Aktiengesellschaft Fungicidal mixtures of an oxime ether carboxylic acid amide with a morpholine or piperidine derivative
    NZ331766A (en) * 1996-04-26 2000-04-28 Basf Ag Fungicide mixtures comprising an oxime ether, a carbamate and a morpholine or pyridine derivative

    Also Published As

    Publication number Publication date
    CZ341698A3 (en) 1999-02-17
    PT900009E (en) 2002-08-30
    HU225630B1 (en) 2007-05-02
    WO1997040673A1 (en) 1997-11-06
    EA199800896A1 (en) 1999-04-29
    CO4761034A1 (en) 1999-04-27
    CN1106148C (en) 2003-04-23
    KR100432453B1 (en) 2005-01-15
    KR20000065009A (en) 2000-11-06
    TW347311B (en) 1998-12-11
    AU2388797A (en) 1997-11-19
    AU734568B2 (en) 2001-06-14
    JP4170393B2 (en) 2008-10-22
    DK0900009T3 (en) 2002-07-01
    PL187549B1 (en) 2004-07-30
    IL126083A0 (en) 1999-05-09
    CN1216438A (en) 1999-05-12
    PL329506A1 (en) 1999-03-29
    EA001006B1 (en) 2000-08-28
    SK282795B6 (en) 2002-12-03
    NZ331766A (en) 2000-04-28
    ATE214874T1 (en) 2002-04-15
    ES2175396T3 (en) 2002-11-16
    JP2000509053A (en) 2000-07-18
    AR006863A1 (en) 1999-09-29
    HUP9903739A3 (en) 2001-08-28
    UA56167C2 (en) 2003-05-15
    CZ291462B6 (en) 2003-03-12
    CA2252523C (en) 2007-07-10
    DE59706770D1 (en) 2002-05-02
    IL126083A (en) 2002-03-10
    HUP9903739A2 (en) 2000-03-28
    US6136802A (en) 2000-10-24
    SK138498A3 (en) 1999-04-13
    CA2252523A1 (en) 1997-11-06
    BR9708874A (en) 1999-08-03
    SI0900009T1 (en) 2002-08-31
    EP0900009A1 (en) 1999-03-10

    Similar Documents

    Publication Publication Date Title
    EP0900021B1 (en) Fungicide mixture
    EP0989806B1 (en) Fungicide mixtures
    EP0982994B1 (en) Fungicidal mixtures
    EP0900009B1 (en) Fungicide mixtures
    EP0906017B1 (en) Fungicide mixtures
    EP0901322B1 (en) Fungicidal mixtures
    EP0900008B1 (en) Fungicidal mixtures
    EP0900019B1 (en) Fungicide mixtures
    EP1353557A1 (en) Fungicidal mixture
    EP0900020B1 (en) Fungicidal mixtures
    EP0984696B1 (en) Fungicidal mixtures
    EP0984695B1 (en) Fungicidal mixtures
    EP0900013B1 (en) Fungicide mixtures
    EP0900011B1 (en) Fungicide mixtures
    EP0984687B1 (en) Fungicidal mixtures
    EP0900012B1 (en) Fungicide mixtures
    EP0912088B1 (en) Fungicidal mixtures
    EP0900018B1 (en) Fungicide mixtures
    EP0892603B1 (en) Fungicidal mixtures
    WO1998008384A1 (en) Fungicidal mixtures
    DE10144991A1 (en) Synergistic mixture of fungicides, useful in plant protection, comprise carbamate or phenylacetic acid derivative strobilurin compound, e.g. carbamates and/or phenylacetic acid derivatives and dithianon
    WO2002054871A1 (en) Fungicide mixtures
    EP0984690B1 (en) Fungicidal mixture
    WO1997040677A1 (en) Fungicide mixtures
    WO2002049438A2 (en) Carbamate-based fungicidal mixtures

    Legal Events

    Date Code Title Description
    PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

    Free format text: ORIGINAL CODE: 0009012

    17P Request for examination filed

    Effective date: 19980903

    AK Designated contracting states

    Kind code of ref document: A1

    Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI NL PT SE

    AX Request for extension of the european patent

    Free format text: SI PAYMENT 980903

    GRAG Despatch of communication of intention to grant

    Free format text: ORIGINAL CODE: EPIDOS AGRA

    17Q First examination report despatched

    Effective date: 20010627

    GRAG Despatch of communication of intention to grant

    Free format text: ORIGINAL CODE: EPIDOS AGRA

    GRAH Despatch of communication of intention to grant a patent

    Free format text: ORIGINAL CODE: EPIDOS IGRA

    GRAH Despatch of communication of intention to grant a patent

    Free format text: ORIGINAL CODE: EPIDOS IGRA

    REG Reference to a national code

    Ref country code: GB

    Ref legal event code: IF02

    GRAA (expected) grant

    Free format text: ORIGINAL CODE: 0009210

    AK Designated contracting states

    Kind code of ref document: B1

    Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI NL PT SE

    AX Request for extension of the european patent

    Free format text: SI PAYMENT 19980903

    REF Corresponds to:

    Ref document number: 214874

    Country of ref document: AT

    Date of ref document: 20020415

    Kind code of ref document: T

    REG Reference to a national code

    Ref country code: CH

    Ref legal event code: EP

    REG Reference to a national code

    Ref country code: CH

    Ref legal event code: NV

    Representative=s name: SCHMAUDER & PARTNER AG PATENTANWALTSBUERO

    REF Corresponds to:

    Ref document number: 59706770

    Country of ref document: DE

    Date of ref document: 20020502

    REG Reference to a national code

    Ref country code: IE

    Ref legal event code: FG4D

    Free format text: GERMAN

    REG Reference to a national code

    Ref country code: DK

    Ref legal event code: T3

    REG Reference to a national code

    Ref country code: PT

    Ref legal event code: SC4A

    Free format text: AVAILABILITY OF NATIONAL TRANSLATION

    Effective date: 20020524

    REG Reference to a national code

    Ref country code: GR

    Ref legal event code: EP

    Ref document number: 20020402013

    Country of ref document: GR

    ET Fr: translation filed
    REG Reference to a national code

    Ref country code: ES

    Ref legal event code: FG2A

    Ref document number: 2175396

    Country of ref document: ES

    Kind code of ref document: T3

    PLBE No opposition filed within time limit

    Free format text: ORIGINAL CODE: 0009261

    STAA Information on the status of an ep patent application or granted ep patent

    Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

    26N No opposition filed

    Effective date: 20021230

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: CP

    Free format text: PRODUCT NAME: PYRACLOSTROBINE; FENPROPIMORPHE; REGISTRATION NO/DATE: 2020023 20030904

    Spc suppl protection certif: 04C0003

    Filing date: 20040304

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: C1

    Free format text: 04C0003, 20040304

    Spc suppl protection certif: 04C0003

    Filing date: 20040304

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: CP

    REG Reference to a national code

    Ref country code: SI

    Ref legal event code: IF

    REG Reference to a national code

    Ref country code: FI

    Ref legal event code: SPCF

    Spc suppl protection certif: K20050001

    REG Reference to a national code

    Ref country code: IE

    Ref legal event code: SPCF

    Free format text: SPC019/2006, 20060629

    Spc suppl protection certif: SPC019/2006

    Filing date: 20060629

    REG Reference to a national code

    Ref country code: IE

    Ref legal event code: SPCG

    Free format text: SPC019/2006:, EXPIRES: 20180903

    Spc suppl protection certif: SPC019/2006

    Expiry date: 20180903

    REG Reference to a national code

    Ref country code: CH

    Ref legal event code: PCAR

    Free format text: SCHMAUDER & PARTNER AG PATENT- UND MARKENANWAELTE VSP;ZWAENGIWEG 7;8038 ZUERICH (CH)

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: AV

    Spc suppl protection certif: 04C0003

    Ref country code: FR

    Ref legal event code: C2

    Free format text: PRODUCT NAME: PYRACLOSTROBINE/FENPROPIMORPHE; REGISTRATION NO/DATE IN FRANCE: 2020023 DU 20030904; REGISTRATION NO/DATE AT EEC: 2020023 DU 20030904

    Spc suppl protection certif: 04C0003

    Filing date: 20040304

    Extension date: 20180904

    Ref country code: FR

    Ref legal event code: AV

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: PLFP

    Year of fee payment: 19

    REG Reference to a national code

    Ref country code: SI

    Ref legal event code: KO00

    Effective date: 20151215

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: PLFP

    Year of fee payment: 20

    PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

    Ref country code: NL

    Payment date: 20160426

    Year of fee payment: 20

    PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

    Ref country code: CH

    Payment date: 20160426

    Year of fee payment: 20

    Ref country code: IE

    Payment date: 20160429

    Year of fee payment: 20

    Ref country code: GB

    Payment date: 20160502

    Year of fee payment: 20

    Ref country code: GR

    Payment date: 20160504

    Year of fee payment: 20

    Ref country code: ES

    Payment date: 20160518

    Year of fee payment: 20

    Ref country code: FI

    Payment date: 20160429

    Year of fee payment: 20

    PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

    Ref country code: AT

    Payment date: 20160502

    Year of fee payment: 20

    Ref country code: FR

    Payment date: 20160428

    Year of fee payment: 20

    Ref country code: IT

    Payment date: 20160428

    Year of fee payment: 20

    Ref country code: DK

    Payment date: 20160426

    Year of fee payment: 20

    Ref country code: SE

    Payment date: 20160429

    Year of fee payment: 20

    Ref country code: BE

    Payment date: 20160427

    Year of fee payment: 20

    Ref country code: PT

    Payment date: 20160418

    Year of fee payment: 20

    PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

    Ref country code: DE

    Payment date: 20160630

    Year of fee payment: 20

    REG Reference to a national code

    Ref country code: DE

    Ref legal event code: R071

    Ref document number: 59706770

    Country of ref document: DE

    REG Reference to a national code

    Ref country code: DK

    Ref legal event code: EUP

    Effective date: 20170422

    REG Reference to a national code

    Ref country code: NL

    Ref legal event code: MK

    Effective date: 20170421

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: SPAY

    Free format text: PRODUCT NAME: PYRACLOSTROBINE; FENPROPIMORPHE; REGISTRATION NO/DATE: 2020023 20030904

    Spc suppl protection certif: 04C0003

    Filing date: 20040304

    Year of fee payment: 1

    Extension date: 20180904

    REG Reference to a national code

    Ref country code: CH

    Ref legal event code: PL

    REG Reference to a national code

    Ref country code: GB

    Ref legal event code: PE20

    Expiry date: 20170421

    REG Reference to a national code

    Ref country code: IE

    Ref legal event code: MK9A

    REG Reference to a national code

    Ref country code: AT

    Ref legal event code: MK07

    Ref document number: 214874

    Country of ref document: AT

    Kind code of ref document: T

    Effective date: 20170422

    REG Reference to a national code

    Ref country code: ES

    Ref legal event code: FD2A

    Effective date: 20170728

    PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

    Ref country code: IE

    Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

    Effective date: 20170422

    Ref country code: GB

    Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

    Effective date: 20170421

    PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

    Ref country code: PT

    Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

    Effective date: 20170505

    PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

    Ref country code: ES

    Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

    Effective date: 20170423

    REG Reference to a national code

    Ref country code: FR

    Ref legal event code: SPAY

    Free format text: PRODUCT NAME: PYRACLOSTROBINE; FENPROPIMORPHE; REGISTRATION NO/DATE: 2020023 20030904

    Spc suppl protection certif: 04C0003

    Filing date: 20040304

    Year of fee payment: 2

    Extension date: 20180904